Exam 19: Aldehydes and Ketones: Nucleophilic Addition Reactions

Exhibit 19-10 Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114,α-cleavage fragment at m/z = 71, no McLafferty rearrangement fragment ¹H NMR: Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS -Refer to Exhibit 19-10.Interpret the mass spectral data for this compound.

Exhibit 19-4 α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon,as shown below. -Refer to Exhibit 19-4.This reaction is called _____ reaction.

​Draw the mechanism of the nucleophilic addition reaction involving acetaldehyde and a neutral nucleophile,in acidic conditions.

Exhibit 19-1 Consider the reaction below to answer the following question(s): -Refer to Exhibit 19-1.Write the complete stepwise mechanism for the reaction shown above.Show all intermediate structures and all electron flow with arrows.

Exhibit 19-1 Consider the reaction below to answer the following question(s): -Refer to Exhibit 19-1.The substance formed on addition of water to an aldehyde or ketone is called a hydrate or a/an:

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Draw: benzophenone

Exhibit 19-10 Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114,α-cleavage fragment at m/z = 71, no McLafferty rearrangement fragment ¹H NMR: Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS -Refer to Exhibit 19-10.Interpret the ¹H NMR spectrum.

If the following substance were treated with HCN followed by aqueous acid and heat, which of the following would be produced? Atoms other than carbon and hydrogen are labeled.

Exhibit 19-3 Consider the reaction below to answer the following question(s). -Refer to Exhibit 19-3.The catalyst in this reaction is:

Exhibit 19-2 Consider the data below to answer the following question(s). Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and aldehydes.The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid.Nitriles can also be hydrolyzed to carboxylic acids using aqueous base.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. -Refer to Exhibit 19-2.The reaction of benzaldehyde with hydrogen cyanide is catalyzed by the addition of a small amount of KCN.Write the complete reaction mechanism for the KCN-catalyzed reaction.Show all electron flow with arrows and show all intermediate structures.

Exhibit 19-9 Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114,α-cleavage fragment at m/z = 71, McLafferty rearrangement fragment at m/z = 86. ¹H NMR: 0.92 δ (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet) -Refer to Exhibit 19-9.Interpret the ¹H NMR data.

Exhibit 19-2 Consider the data below to answer the following question(s). Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and aldehydes.The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid.Nitriles can also be hydrolyzed to carboxylic acids using aqueous base.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. -Refer to Exhibit 19-2.The reaction of an aldehyde with hydrogen cyanide is an example of _____ reaction.

Based only on the spectrum below,what is inferred about the compound used to produce the spectrum?

Exhibit 19-9 Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114,α-cleavage fragment at m/z = 71, McLafferty rearrangement fragment at m/z = 86. ¹H NMR: 0.92 δ (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet) -Refer to Exhibit 19-9.Interpret the mass spectral data.

Which of the following reagents could be used to convert 3-cyclopentyl-2-methylpropanal to the following substance? Atoms other than carbon and hydrogen are labeled.

Name the following compound.Atoms other than carbon and hydrogen are labeled.

Name:

Exhibit 19-3 Consider the reaction below to answer the following question(s). -Refer to Exhibit 19-3.The nucleophile in this reaction is:

Consider the following structure.Atoms other than carbon and hydrogen are labeled. Oxidation of this compound yields: